CISO Tribune

Vendor comparison · 2 companies

Cayosoft vs Obsidian Security

Cayosoft sells products for managing and protecting Microsoft environments, covering security and control across Active Directory, Azure AD, Microsoft 365 and Exchange Online. Obsidian Security sells real-time visibility, continuous governance and runtime enforcement over agents, identities and integrations across third-party apps. CISO Tribune files both under Identity threat detection and response. This page sets the two records side by side: what each sells, where it is based, who owns and funds it, the customers it names and its recent news, each fact numbered to its source.

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  • Cayosoft
  • Obsidian Security
Cayosoft vs Obsidian Security: Products, Customers and Funding Compared
CayosoftCayosoft sells products for managing and protecting Microsoft environments, covering security and control across Active Directory, Azure AD, Microsoft 365 and Exchange Online.cayosoft.comObsidian SecurityObsidian Security sells real-time visibility, continuous governance and runtime enforcement over agents, identities and integrations across third-party apps.obsidiansecurity.com
What it sells
  • Cayosoft Guardian Audit & Restore[5]Monitors all directory changes and lets administrators roll back those changes.
  • Guardian Protector[4][5]A free, agentless tool for continuous monitoring and real-time threat detection.
  • Cayosoft Management and Protection Suite[6]A suite that includes Cayosoft Administrator and Cayosoft Guardian standard.
  • Cayosoft Group Policy Management[12]Governs, documents and restores GPO changes across every domain.
  • Continuous GovernanceChecks each requirement, written once, in each connected app that exposes the data it needs.
Categories
Headquarters
Westerville, United States[1]Not stated on its pages
Founded
Not stated on its pagesNot stated on its pages
Ownership and funding
Privately held[4]Privately held[1]
Named customers
Not stated on its pagesNot stated on its pages
Recent news
Not stated on its pages
  • August 4, 2026Obsidian Security said it raised $85 million in a Series D funding round that valued the company at $1.1 billion.[15]
G2 and Gartner Peer Insights
  • G2: Not stated on its pages
  • Gartner Peer Insights: Not stated on its pages
  • G2: Not stated on its pages
  • Gartner Peer Insights: Not stated on its pages
Who it fits
Not written yetFrom its own pages, Obsidian Security sells to security teams that must defend actions by identities they can barely enumerate, across apps they did not build, on infrastructure they do not control. Obsidian Security describes security teams at large financial services and technology companies adopting its product to detect account takeovers, SaaS threats and privilege misuse. Obsidian Security addresses enterprises whose data lives in third-party enterprise apps they do not own. Obsidian Security addresses organisations whose employees connect AI agents to business apps through MCP. Obsidian Security addresses organisations where each team picks its own AI agent tool.
Last verified
September 27, 2026November 4, 2026

Where they overlap

  • Cayosoft and Obsidian Security are both filed under Identity threat detection and response.
  • Both are privately held.

Where they differ, field by field

  • Cayosoft's primary category is Directory backup and recovery; Obsidian Security's is SaaS security posture.
  • Cayosoft is also filed under Identity governance and administration. Obsidian Security is also filed under AI model and agent security and Workforce AI usage security.
  • Cayosoft lists Cayosoft Guardian Audit & Restore, Guardian Protector, Cayosoft Management and Protection Suite and Cayosoft Group Policy Management. Obsidian Security lists Continuous Governance.
  • Cayosoft is headquartered in Westerville, United States.

What it sells: Cayosoft

What Cayosoft Guardian Audit & Restore does[5]
Cayosoft Guardian Audit & Restore monitors all directory changes and lets administrators roll back those changes. Cayosoft Guardian Audit & Restore is for recovering and protecting Active Directory and hybrid AD data.
What Cayosoft Management and Protection Suite does[6]
The Cayosoft Management and Protection Suite includes Cayosoft Administrator and Cayosoft Guardian standard, to manage, monitor and recover hybrid Microsoft directories, users, groups and other critical objects and settings. The suite can be expanded by adding Cayosoft Guardian Forest Recovery, which protects Active Directory from ransomware and other full forest directory outages.
What Cayosoft Group Policy Management does[12]
Cayosoft Group Policy Management governs, documents and restores GPO changes across every domain. Each GPO moves through edit, check-in, submit, approve and deploy steps so that only approved policy reaches Active Directory. Each checked-in version is archived rather than overwritten, supporting comparison, documentation, rollback to a known-good state and audit review.

What it sells: Obsidian Security

What Continuous Governance does
The control model includes mappings to NIST, CIS, ISO 27001, and GDPR. Supported controls are checked continuously, and changes are shown. Fixes are routed through Jira, ServiceNow, and other supported tools.

Questions about Cayosoft and Obsidian Security

What do Cayosoft and Obsidian Security sell?
Cayosoft sells Cayosoft Guardian Audit & Restore, Guardian Protector, Cayosoft Management and Protection Suite and Cayosoft Group Policy Management. Obsidian Security sells Continuous Governance.
Are Cayosoft and Obsidian Security in the same category?
They share Identity threat detection and response. Cayosoft's primary category is Directory backup and recovery and Obsidian Security's is SaaS security posture.
Where are Cayosoft and Obsidian Security headquartered?
Cayosoft is headquartered in Westerville, United States.
Who owns Cayosoft and Obsidian Security?
Cayosoft is privately held. Obsidian Security is privately held.
Who are Cayosoft and Obsidian Security sold to?
From its own pages, Obsidian Security sells to security teams that must defend actions by identities they can barely enumerate, across apps they did not build, on infrastructure they do not control.
What have Cayosoft and Obsidian Security announced recently?
August 4, 2026: Obsidian Security said it raised $85 million in a Series D funding round that valued the company at $1.1 billion.

About Cayosoft

Cayosoft sells products for managing and protecting Microsoft environments, covering security and control across Active Directory, Azure AD, Microsoft 365 and Exchange Online. Cayosoft products are designed for any step in the journey to Microsoft 365. Cayosoft solutions are purpose-built to help manage and protect Microsoft environments that are on-premises, hybrid or Microsoft 365-only. Cayosoft licenses its products by subscription.[5][6]

Cayosoft Administrator offers role-based delegation, rule-based automation, self-service and Microsoft 365 license optimization. Cayosoft Administrator enables IT teams to manage hybrid environments through a single interface. Cayosoft Administrator is a unified TrueHybrid management solution for control over administrators and help desk staff who make changes to Microsoft enterprise systems. Granular Roles and Rules limit administrators to authorized tasks.[5][7]

Cayosoft Administrator comes with more than 125 pre-built templates and requires no extra SQL, LDAP or synchronization. Administrators can run real-time reports on Office 365 or schedule those reports for e-mail delivery, local storage or shared storage. Cayosoft provides pre and post-collection filtering, and reports can be viewed in email, Excel or CSV. Cayosoft offers user-enabled password resets so that users can remedy lockouts without IT assistance. Direct report management lets users update their own attributes and those of subordinates in a web-based self-service portal. Cayosoft puts on-premises AD and Office 365 into one interface for help desk admins, with filtered access to only the necessary tasks.[8][9]

Inclusion Rules define the list of users that must be in a group, and Exclusion Rules define the list of users who should never be in it. Group membership updates can be triggered by events like user provisioning or user deprovisioning, or run on a schedule. Built-in group membership queries can be added to group membership rules to update any Microsoft group type, from Active Directory and Exchange to Azure AD and Microsoft 365 Groups. Self-service group management lets distribution list, application and data owners manage who has access to their resources. Cayosoft Administrator brings Teams administration with delegation, automatically updated groups and Teams membership, telephony management and policy assignment control. Cayosoft manages the available phone numbers, reclaims numbers when users leave and assigns Teams user policies required for Direct Routing. Cayosoft can alert and roll back undesired changes when they are detected.[10][11]

Cayosoft Guardian Audit & Restore monitors all directory changes and lets administrators roll back those changes. Recovery scenarios covered include AD object and attribute, partition, domain controller and forest recovery. Cayosoft supports cutting over to a clean, isolated, standby forest. Guardian Protector is a free, agentless tool that delivers continuous monitoring, real-time threat detection and audit-ready visibility across Active Directory, Microsoft Entra ID and key Microsoft 365 services, without time limits or object caps. Cayosoft monitors human and non-human identity activity and supports rollback.[2][5]

The Cayosoft Management and Protection Suite is purpose-built for modern Microsoft environments. The Cayosoft Management and Protection Suite includes Cayosoft Administrator and Cayosoft Guardian standard, to manage, monitor and recover hybrid Microsoft directories, users, groups and other critical objects and settings. The suite can be expanded by adding Cayosoft Guardian Forest Recovery, which protects Active Directory from ransomware and other full forest directory outages.[5][6]

Cayosoft Group Policy Management governs, documents and restores GPO changes across every domain. Each GPO moves through edit, check-in, submit, approve and deploy steps so that only approved policy reaches Active Directory. Active Directory remains unchanged until an approved version is explicitly deployed. Each checked-in version is archived rather than overwritten, supporting comparison, documentation, rollback to a known-good state and audit review. Editing, approval and export or deployment rights can be assigned to different users or groups. Microsoft ended support for Advanced Group Policy Management (AGPM) on April 14, 2026, with no direct successor. Cayosoft provides a supported approach to Group Policy management with check-in and check-out, approvals, version control, role delegation, analysis, rollback and multi-domain governance.[12]

Cayosoft serves school districts and universities of all sizes, for students, faculty and staff. Cayosoft Administrator provides automated account provisioning and deprovisioning, group management, role-based delegation and group-based license assignment. A large U.S. state replaced a legacy AD management tool with Cayosoft Administrator. The IRS consolidated multiple identity management tools into Cayosoft.[2][3][13][14]

Cayosoft on the record

Sources

Cayosoft full record

  1. [1]AboutCayosoft · cayosoft.com · undated page, accessed September 27, 2026 · Tier A
  2. [2]cayosoft.comCayosoft · cayosoft.com · undated page, accessed September 27, 2026 · Tier A
  3. [3]Cayosoft achieves record sales company growthCayosoft · cayosoft.com · published April 17, 2024 · Tier A
  4. [4]Cayosoft – Hybrid Active Directory Management & Recovery PlatformCayosoft · undated page, accessed October 23, 2026 · Tier A
  5. [5]Products - CayosoftCayosoft · undated page, accessed November 10, 2026 · Tier A
  6. [6]Manage and Protect Microsoft AD and O365 for EnterprisesCayosoft · undated page, accessed November 10, 2026 · Tier A
  7. [7]Hybrid Active Directory and Office 365 AdministrationCayosoft · undated page, accessed November 10, 2026 · Tier A
  8. [8]Active Directory Reporting - Unified AD ReportingCayosoft · undated page, accessed November 10, 2026 · Tier A
  9. [9]Hybrid Microsoft AD Self-Service and Help DeskCayosoft · undated page, accessed November 10, 2026 · Tier A
  10. [10]Dynamic Groups - CayosoftCayosoft · undated page, accessed November 10, 2026 · Tier A
  11. [11]Microsoft Teams ManagementCayosoft · undated page, accessed November 10, 2026 · Tier A
  12. [12]Group Policy Management That Controls Every Change | Cayosoft Group Policy ManagementCayosoft · undated page, accessed November 10, 2026 · Tier A
  13. [13]Manage and Protect Microsoft AD and O365 for K-12 school districts and higher educationCayosoft · undated page, accessed November 10, 2026 · Tier A
  14. [14]Manage and Protect Microsoft AD and O365 for state, local and federal governmentCayosoft · undated page, accessed November 10, 2026 · Tier A

Obsidian Security full record

  1. [1]obsidiansecurity.comObsidian Security · obsidiansecurity.com · undated page, accessed November 4, 2026 · Tier A
  2. [2]Unlocking ai potential securelyObsidian Security · obsidiansecurity.com · undated page, accessed November 4, 2026 · Tier A
  3. [3]Secure AI. Fearless Innovation. | ObsidianObsidian Security · undated page, accessed November 10, 2026 · Tier A
  4. [4]The Obsidian Security PlatformObsidian Security · undated page, accessed November 10, 2026 · Tier A
  5. [5]Obsidian Security – Who We AreObsidian Security · undated page, accessed November 10, 2026 · Tier A
  6. [6]The Data Behind Better SecurityObsidian Security · undated page, accessed November 10, 2026 · Tier A
  7. [7]Network EffectsObsidian Security · undated page, accessed November 10, 2026 · Tier A
  8. [8]Automate Third-Party Application ComplianceObsidian Security · undated page, accessed November 10, 2026 · Tier A
  9. [9]Runtime Policy Decision Engine for AI Agents | Obsidian SecurityObsidian Security · undated page, accessed November 10, 2026 · Tier A
  10. [10]MCP Security Proxy for AI Agents | Obsidian SecurityObsidian Security · undated page, accessed November 10, 2026 · Tier A
  11. [11]MCP Security: Audit and Control Every MCP ServerObsidian Security · undated page, accessed November 10, 2026 · Tier A
  12. [12]Continuous Third-Party App Governance | Obsidian SecurityObsidian Security · undated page, accessed November 10, 2026 · Tier A
  13. [13]Third-Party Application Security | Obsidian SecurityObsidian Security · undated page, accessed November 10, 2026 · Tier A
  14. [14]Flexible SaaS Security Pricing | ObsidianObsidian Security · undated page, accessed November 10, 2026 · Tier A
  15. [15]Obsidian Security raises funding at $1.1 billion valuation on AI security demand | ReutersReuters · published August 4, 2026 · Tier B

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